New Baeyer—Villiger rearrangement products in the addition of singlet oxygen to furfuryl acetate and furfuryl benzoate

Kuo, Yueh‐Hsiung; Shih, Kao-Shang; Lee, Shu-Mei

doi:10.1016/1010-6030(88)80119-9

Cited by 5 publications

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Oxidative Cleavage of Furans

Merino

2015

Organic Reactions

View full text Add to dashboard Cite

Oxidative ring cleavage reactions of furans constitute a group of important transformations that have found wide utility in synthetic organic chemistry. These processes have been used to prepare a variety of 1,4‐dicarbonyl compounds including 1,4‐dioxoalkenes, 4‐oxoalkenals, 4‐oxoalkenoic acids, and their derivatives such as 4‐hydroxybutenolides and 2,5‐dialkoxydihydrofurans. Oxidations of furfuryl alcohols (Achmatowicz reaction) and furfuryl amines (aza‐Achmatowicz reaction) provide access to highly functionalized heterocyclic structures that have been employed as intermediates in synthetic routes for the preparation of complex molecules including carbohydrates and alkaloids. Complete oxidative degradation of the furan ring affords carboxylic acids; thus the oxygen heterocycle has served as a masked carboxyl group in many synthetic studies. These transformations and their applications in total syntheses are covered in this chapter.

show abstract

Oxidative Cleavage of Furans

Merino

2015

Organic Reactions

View full text Add to dashboard Cite

show abstract

Baeyer‐Villiger Oxidation

2010

Comprehensive Organic Name Reactions and Reagents

View full text Add to dashboard Cite

Oxidation of ketones or cyclic ketones into esters or lactones by peracids or hydrogen peroxide is known as the Baeyer–Villiger oxidation. Some of the typical peracids have been found to involve in this type of the reaction are peroxybenzoic acid, m ‐chloroperoxybenzoic acid ( m CPBA), peroxyacetic acid, and trifluoroperoxyacetic acid. In this reaction the substituted group often migrates in the following order: tertiary > secondary > cyclohexyl > benzyl >phenyl > primary > methyl and stereochemistry and chirality of the migrating group are retained during the reaction. This reaction has wide application in the synthesis of esters and lactones.This reaction has been extensively reviewed and modified using bis[trimethylsilyl]peroxide or basic hydrogen peroxide.

show abstract

Singlet‐Oxygen Oxidation of 5‐Hydroxymethylfurfural in Continuous Flow

2014

View full text Add to dashboard Cite

Singlet-oxygen oxidation of 5-hydroxymethylfurfural (5-HMF) was performed in continuous flow mode using rose Bengal as photosensitizer. The resulting butenolide (H(2) MF) was formed selectively in high yield. The procedure proved to be scalable and applicable to related bio-based furfurals. Furthermore, preliminary data show that H(2) MF can be readily isomerized thermally to 5-hydroxy-4-keto-pentenoic acid oligomers.

show abstract

New Baeyer—Villiger rearrangement products in the addition of singlet oxygen to furfuryl acetate and furfuryl benzoate

Cited by 5 publications

References 36 publications

Oxidative Cleavage of Furans

Oxidative Cleavage of Furans

Baeyer‐Villiger Oxidation

Singlet‐Oxygen Oxidation of 5‐Hydroxymethylfurfural in Continuous Flow

Contact Info

Product

Resources

About